3-Acylindoles via a one-pot, regioselective Friedel-Crafts reaction

被引:49
作者
Wynne, JH
Lloyd, CT
Jensen, SD
Boson, S
Stalick, WM [1 ]
机构
[1] George Mason Univ, Dept Chem, Fairfax, VA 22030 USA
[2] USN, Res Lab, Div Chem, Washington, DC 20375 USA
来源
SYNTHESIS-STUTTGART | 2004年 / 14期
关键词
indole; regioselectivity; Friedel-Crafts reactions; acylations;
D O I
10.1055/s-2004-831177
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Within we report a general one-pot high-yielding Friedel-Crafts acylation of indole using acid chlorides and diethylaluminum chloride in gram scale quantities. This general synthesis affords products that are easily isolated and require no complex purification procedures.
引用
收藏
页码:2277 / 2282
页数:6
相关论文
共 36 条
  • [1] NOVEL SYNTHESIS OF HETEROCYCLIC KETONES
    ANTHONY, WC
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1960, 25 (11) : 2049 - 2053
  • [2] 12-acylindolo[1,2-c]quinazolines by palladium-catalyzed cyclocarbonylation of o-alkynyltrifluoroacetanilides
    Battistuzzi, G
    Cacchi, S
    Fabrizi, G
    Marinelli, F
    Parisi, LM
    [J]. ORGANIC LETTERS, 2002, 4 (08) : 1355 - 1358
  • [3] Chemoselective radical cleavage of Cbz-protected nitrogen compounds
    Bennasar, ML
    Roca, T
    Padullés, A
    [J]. ORGANIC LETTERS, 2003, 5 (04) : 569 - 572
  • [4] Generation and intermolecular reactions of 3-indolylacyl radicals
    Bennasar, ML
    Roca, T
    Griera, R
    Bassa, M
    Bosch, J
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (17) : 6268 - 6271
  • [5] Bergman J, 1996, HETEROCYCL COMMUN, V2, P305
  • [6] SYNTHESIS AND REACTIONS OF SOME 3-(2-HALOACYL)INDOLES
    BERGMAN, J
    BACKVALL, JE
    LINDSTRO.JO
    [J]. TETRAHEDRON, 1973, 29 (07) : 971 - 976
  • [7] INTRAMOLECULAR RING-CLOSURE OF ALPHA,BETA-UNSATURATED 3-ACYLINDOLES
    BERGMAN, J
    VENEMALM, L
    [J]. TETRAHEDRON LETTERS, 1987, 28 (32) : 3741 - 3744
  • [8] ELECTROPHILIC SUBSTITUTION IN INDOLES .V. INDOLENINES AS INTERMEDIATES IN BENZYLATION OF 3-SUBSTITUTED INDOLES
    BISWAS, KM
    JACKSON, AH
    [J]. TETRAHEDRON, 1969, 25 (01) : 227 - &
  • [9] BUUHOI NP, 1949, RECL TRAV CHIM PAY B, V68, P5
  • [10] UNUSUAL SITE OF ELECTROPHILIC ATTACK ON INDOLE AND CARBAZOLE
    CIPICIANI, A
    CLEMENTI, S
    LINDA, P
    SAVELLI, G
    SEBASTIANI, GV
    [J]. TETRAHEDRON, 1976, 32 (21) : 2595 - 2597